Cyclo-hexylidene ethyl cyanoacetate as an insecticide



Patented Jan. 5, 1943 UNlTEl) STATES crow-- nnxnmnmtn'rm CYANOACE- ran: as an msnc'rrcmn William" Moore, Stamford, Conn, aasignor to American Cyanamid Company, New York, N, Y.-, a corporation of Maine No Drawing. Application mm 7, 1941,

Serial No. 382,171

i ends. (01. 101-4 The presentinvention relates to a pest-control agent and. more particularly to a compound which is especially eflective as a contact poison for the control of insects and allied pests.

I have discovered that cyclohexylidene ethyl 5 cyanoacetate possesses strong insecticidal activity against sucking and soft-bodied insects which are particularly difllcult to exterminate, for example the'citrusred spider, Tetramlchus citri,

and the bean aphid, Aphis rumicis.

The following example illustrates a specific method of preparing the above compound in ac- .cordance with theinvention. Materials employed are in parts by weight.

Example A mixture consisting of 46 parts oi ethyl eyanoacetate, 40 parts of ,cyclohexanone and one. parts of piperidine (catalyst) was allowed to standfor 12 hours in a closed vessel at room temper- 20 We the invention has been described ature (20 0 Considerable water had separatedat the end of this period. The mixture was then heated for two hours upon a steam bath.' The reaction product was dissolved in ether. washed "neutral (0.05% H2804). dried over sodium suliate and distilled at reduced pressure. Thecyclohexylidene ethyl cyanoacetate was recovered as a colorless liquid boiling at 121' O.

- at less thanlmmpressura v Spray solutions were prepared by dissolving the go cyclohexylidene. ethyl cyanoacetate in a solvent medium consisting of 65% acetone and 35% water. A 99.4% control was obtained when a spray of 1-1000 dilutionwasused against the citrus red spider, Tetranuchus citri. At a dilution oi 14500, the insecticide gave a 91% control on the bean aphid, Aphis remicis.

Although the compound of this invention is especially eilective as a contact poison for the 10 control of insect pests, it may also be used forfungicidal-and bactericidal purposes. 1 This new insecticide may be applied in any of the conventional manners. Thus, for example,

it may be used in an aqueous emulsion or incor- 1 5 poratedin organic liquids such as the aliphatic and aromatic hydrocarbons 'for spraying purposes, or it may be effectively used in dusts with such inert solid .diluents as meselguhr, wood flour ,v walnut shell, talc, and the like. th

particular reference to c emhod-iments, it is to be understood that it is not to be limited thereto but is to be lu'oadly'construed and re* I claim: r v An insecticide containing as an active ingredlent cyclohexylldene ethyl .cyanoacetate.

' wnnm MOORE.

solelyby. the scope oi the appended 

